Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition

A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed. Addition of carbonyl compounds which contain bulky adamantyl substituent and beta-keto or phosphonate group to conjugated alpha-bromonitroolefins in the presence of a chiral Ni(II) complex gave corresponding non-racemic products of Michael reaction. These adducts were used for intramolecular cyclization leading to trans-4,5-dihydrofurans with two stereocenters. Resulting trans4,5-dihydrofurans were obtained in good yields with moderate to high enantioselectivities (84-99% ee) and excellent diastereoselectivities (dr >99%). (c) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed, resulting in good yields with moderate to high enantioselectivities (84-99% ee) and excellent diastereoselectivities (dr >99%).